A CEO’s Playbook To Supercharge Your Next Offsite

Dan Schoenbaum
8 min readOct 25, 2022


Now that the risks of Covid-19 are largely manageable, it’s a great opportunity to bring your team back together for the ever-critical team offsite. For the past several years, this essential activity has been largely relegated to less effective, Zoom-based events. These stop-gap opportunities to focus on planning and virtual “team building” while wine tasting were never productive and — at best — tolerable.

As a former Cybersecurity and Enterprise software CEO and COO, I have led and participated in countless offsites over my multi-decade career. I’d like to share critical strategies learned through several, “game-changing” offsites, and — of course — a few along the way that were painfully bad. As they say, you learn just as much, if not more, from life’s failures.

With teams working remotely, many of your employees may not have spent critical time together, hindering team dynamics. Thus, an important element of a team offsite is the social aspect of convening your team, bonding and establishing the firm foundations required to work together.

However, the purpose of this article is to focus on the “work” portion of the meeting. My goal is to help you run a better meeting, get aligned on critical strategies, and better operationalizing both the meeting and the ever-critical process and execution following the meeting.

Companies often gather for shorter, quarterly business reviews (QBR) meetings and pipeline reviews. I consider that working IN the business, and 80–90% of your time as leaders is typically spent here. Conversely, the goal of the strategic offsite is to get away from day-to-day distractions and think exponentially, set strategic direction and gain alignment on future strategies. This should be considered working ON the business, and your meeting should avoid any drift away from this level of critical thinking.

Before The Meeting: Preparation makes for a more productive session

  1. Team introspection: Ask your team to reflect back on the previous quarter(s) or the year. Survey them with a simple Google Form asking for their perspective. Depending on your situation, you may want to ask what accomplishments they are proud of, areas where they feel the team can improve or feelings about the culture of your team or company. Gathering this information ahead of your meeting helps you understand the audience, prevents “groupthink”, and allows participants to share their feedback with the team, which makes for a more productive, and authentic meeting.
  2. Level set with relevant analysis: Often missing prior to an offsite is a pre-briefing with helpful information to help drive more effective decision making. One example: customer data.

- The voice of the customer. This information isn’t often widely understood across executive teams. What is the “temperature” of your top 10 customers? Are they expanding, contracting? What are they happy/unhappy about? What can everyone learn from customer churn? This is critical information you should all know, at all times, whether you are at an offsite, or not.

- Competitive analysis: Markets are dynamic, depending on your company and the market, your toughest competitors may be moving faster than you are. Make sure your executive team and key managers know who they are up against, their strengths, lessons to learn from them, and — most important — where the whitespace lies to win big.

3. Take the temperature: Ask your leadership and broader team what is top of mind for them. What are the key topics they want to cover in the meeting? Are there pressing items they feel urgency to discuss and resolve? Be sure to engage them with planning, and get the team excited about the offsite and before you even get together in person.

4. Assign any critical pre-work — asking your team to come prepared with plans, ideas and even presentations makes the meeting more productive, especially if teams work collaboratively prior to your meeting.

5. Be clear about goals for the offsite, and create an agenda that reflects and reinforces those goals. For example: 1) Discuss and debate current opportunities and challenges; 2) Create strategic plans for the future.

The Meeting:

1. Set the stage: Following recommended ice breakers — which actually help put teams at ease, initiate the meeting by setting the stage. Begin with the “end” in mind. Good example: We are here to define the 5 key growth initiates for our company in 2023, document the specific plans to execute and establish the metrics to measure the success. Poor example: This meeting is to help us plan for the next fiscal year.

Pro Tip: When setting the stage, be sure to include the team. Ask team members to complete the following statement:

“I’d be really happy if, by the end of our offsite, we… [add your objective here].

2. Create a safe space: It’s a good idea — and may be comforting to your team — to set ground rules. Make sure everyone knows that the offsite should be a safe space where people can speak up and constructively challenge one another (and you) without any fear of reprisal. It’s also helpful to pledge confidentiality within the meeting space. What is said at the offsite is for you and your team alone, and will not be shared with others in the office — unless the team reaches a consensus about authorizing specific messages or information to be communicated externally.

3. Learn personalities: If you have team disfunction or poor collaboration across your team, I highly recommend exercises to learn about team personalities and working styles. Explore performing a Myers-Briggs assessment, a DiSC analysis, or other psychometric personality analysis. This can help your team understand one another’s personality and working style. It can help highlight employees who will collaborate best with each other, might surface and improve chances of potential conflict, and more — all very valuable insights to strengthening your team and the bonds within it.

a DiSC assessment from a recent offsite yielded valuable insights. The author (shown at the top of the circle), and the teams’ distribution enabled more productive working relationships.

4. Tip for team exercises and planning: Identify the mountain top. I previously served in a military combat unit. One of the most effective leadership traits our officers embraced was to tell us where our field exercise needed to end — usually on a mountain top. However, they never told us what to do or how to get there. If the “destination” is not abundantly clear, your time together will be less fruitful. Don’t constrain a team by trying to tell them “how to get there”. Some of the best learning and collaboration will come from allowing your team the space to work together and create plans and leverage one-another to determine how to get to the desired “destination”.

5. Gather feedback from the team: Offsite meetings are a great opportunity to give and receive feedback about yourself and your working style. Your entire leadership team should do the same. As a CEO, I always volunteered to go first. My approach was simple, everyone got a 3x5 note card and wrote one thing they felt I did well. On the other side was an opportunity to write one thing they would like to see me improve. I left the room and had everyone fill out the cards and put them into a bowl. Members could identify themselves, or remain anonymous. The input I received was invaluable and helped me recognize blind spots, and areas I needed to improve. I still have a folder with screenshots of every note received, and I review them regularly. I highly recommend this exercise for your offsite!

Feedback from my team when I was a first-time CEO. I kept every piece of feedback and review it regularly

6. Operationalize your meeting: Designate a note taker, record all tasks, and ensure a single owner for every task. While this seems obvious, I have attended — and still see — many offsites where much is discussed, and agreed upon, but the meeting is not properly operationalized, and execution and accountability suffer. This impacts team effectiveness, which can erode morale, and trust in leadership. Be sure you focus on the operational aspects of your meeting.

7. You can’t manage what you don’t measure: An important part of this operationalization is to measure the impact of your meeting and any changes made. You will need to define and agree upon the metrics to measure. What are they currently, and what is the intended goal to measure success? Agree to this before your meeting ends, and include an accountability, or “governance” plan. This should include cadence for check-in meetings following the offsite and necessary details to ensure that progress is measured and reported.

8. Get “buy in” — sign the plan: It can be helpful to document your new plan and have the team literally sign the document to gain their commitment. This is especially true if your team is not initially aligned, or your meeting outcome represents a major shift in strategy or direction. In a previous role, our entire executive team came together and created an aggressive growth plan to get us to an IPO. The plan made some uncomfortable and generated a lot of spirited discussion, but — in the end — we all agreed to plans, metrics, milestones, and “locked in” our collective commitment by signing the plan in ink. It was a great tool to foster alignment and unity across the team.

After the meeting:

After your meeting concludes, I recommend sending a survey to your team immediately following the meeting. Don’t wait more than a day to send this, enabling you to capture valuable data while it’s fresh in everyone’s mind. What did they like? What was the most valuable segment of the meeting? What needs to improve next time?

Last, to maximize your results, make sure you schedule a regular cadence meeting to prevent falling back to “business as usual”. This time should be spent communicating the outcome of the meeting beyond your team, tracking the execution and metrics related to your plans and — of course — celebrating your wins.

Now that offsites are back in action, leadership should make the most of what can often be missed in the chaos of massive Zoom meetings. By following even some of these tips, your team will not only be more engaged, aligned, and prepared to better execute, but also grateful for the time spent together. The bonds formed in person can yield amazing results both in terms of relationships and the overall business outcome.

If you have any questions or comments from this article, or want to share any feedback, feel free to drop me a line!



Dan Schoenbaum

2x CEO, 2x COO. Growth expert, GTM & PLG Expert, marathoner, Former IDF Sniper, and Proud Father.